Reduction of antitumour mitosenes in non-aqueous and aqueous environment. An electron spin resonance and cyclic voltammetry study

M. Maliepaard, N.J. de Mol, H.L. Janssen, A R Goeptar, J.M. te Koppele, N P Vermeulen, W. Verboom, David N Reinhoudt

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

Chemical reduction of mitosenes under aerobic conditions in DMSO showed characteristic ESR signals of the mitosene derived semiquinone free radicals. However, these signals diminished strongly upon addition of water to the reaction mixture, indicating a short lifetime of the mitosene semiquinone free radicals under aqueous conditions. In addition, enzymatic one-electron reduction of these mitosenes with either xanthine oxidase or purified NADPH cytochrome P450 reductase under anaerobic conditions showed no signals of the mitosene semiquinone free radicals. Subsequent cyclic voltammetry measurements demonstrated facilitation of the further one-electron reduction of the mitosene semiquinone free radicals in the presence of water in comparison with non-aqueous conditions. The present results strongly suggest that in the presence of water relatively stable hydroquinones are formed upon reduction of mitosenes. Consequently, the steady state concentrations of mitosene semiquinone free radicals will be lowered substantially in aqueous environment. Thus under physiological conditions, two-electron reduction and formation of the mitosene hydroquinone might be important in processes leading to DNA alkylation by these mitosenes.

Original languageEnglish
Pages (from-to)109-21
Number of pages13
JournalFree Radical Research
Volume22
Issue number2
DOIs
Publication statusPublished - Feb 1995

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Electron Spin Resonance Spectroscopy
Cyclic voltammetry
Paramagnetic resonance
Free Radicals
Electrons
Water
Hydroquinones
NADPH-Ferrihemoprotein Reductase
Personal Autonomy
Xanthine Oxidase
Alkylation
Dimethyl Sulfoxide
mitosene
semiquinone radicals
DNA

Keywords

  • Alkylation
  • Animals
  • Antineoplastic Agents
  • Borohydrides
  • DNA
  • Dimethyl Sulfoxide
  • Electron Spin Resonance Spectroscopy
  • Free Radicals
  • Mitomycins
  • NADPH-Ferrihemoprotein Reductase
  • Oxidation-Reduction
  • Quinones
  • Rats
  • Solutions
  • Water
  • Xanthine Oxidase
  • Journal Article
  • Research Support, Non-U.S. Gov't

Cite this

Maliepaard, M. ; de Mol, N.J. ; Janssen, H.L. ; Goeptar, A R ; te Koppele, J.M. ; Vermeulen, N P ; Verboom, W. ; Reinhoudt, David N. / Reduction of antitumour mitosenes in non-aqueous and aqueous environment. An electron spin resonance and cyclic voltammetry study. In: Free Radical Research. 1995 ; Vol. 22, No. 2. pp. 109-21.
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abstract = "Chemical reduction of mitosenes under aerobic conditions in DMSO showed characteristic ESR signals of the mitosene derived semiquinone free radicals. However, these signals diminished strongly upon addition of water to the reaction mixture, indicating a short lifetime of the mitosene semiquinone free radicals under aqueous conditions. In addition, enzymatic one-electron reduction of these mitosenes with either xanthine oxidase or purified NADPH cytochrome P450 reductase under anaerobic conditions showed no signals of the mitosene semiquinone free radicals. Subsequent cyclic voltammetry measurements demonstrated facilitation of the further one-electron reduction of the mitosene semiquinone free radicals in the presence of water in comparison with non-aqueous conditions. The present results strongly suggest that in the presence of water relatively stable hydroquinones are formed upon reduction of mitosenes. Consequently, the steady state concentrations of mitosene semiquinone free radicals will be lowered substantially in aqueous environment. Thus under physiological conditions, two-electron reduction and formation of the mitosene hydroquinone might be important in processes leading to DNA alkylation by these mitosenes.",
keywords = "Alkylation, Animals, Antineoplastic Agents, Borohydrides, DNA, Dimethyl Sulfoxide, Electron Spin Resonance Spectroscopy, Free Radicals, Mitomycins, NADPH-Ferrihemoprotein Reductase, Oxidation-Reduction, Quinones, Rats, Solutions, Water, Xanthine Oxidase, Journal Article, Research Support, Non-U.S. Gov't",
author = "M. Maliepaard and {de Mol}, N.J. and H.L. Janssen and Goeptar, {A R} and {te Koppele}, J.M. and Vermeulen, {N P} and W. Verboom and Reinhoudt, {David N}",
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doi = "10.3109/10715769509147533",
language = "English",
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Reduction of antitumour mitosenes in non-aqueous and aqueous environment. An electron spin resonance and cyclic voltammetry study. / Maliepaard, M.; de Mol, N.J.; Janssen, H.L.; Goeptar, A R; te Koppele, J.M.; Vermeulen, N P; Verboom, W.; Reinhoudt, David N.

In: Free Radical Research, Vol. 22, No. 2, 02.1995, p. 109-21.

Research output: Contribution to JournalArticleAcademicpeer-review

TY - JOUR

T1 - Reduction of antitumour mitosenes in non-aqueous and aqueous environment. An electron spin resonance and cyclic voltammetry study

AU - Maliepaard, M.

AU - de Mol, N.J.

AU - Janssen, H.L.

AU - Goeptar, A R

AU - te Koppele, J.M.

AU - Vermeulen, N P

AU - Verboom, W.

AU - Reinhoudt, David N

PY - 1995/2

Y1 - 1995/2

N2 - Chemical reduction of mitosenes under aerobic conditions in DMSO showed characteristic ESR signals of the mitosene derived semiquinone free radicals. However, these signals diminished strongly upon addition of water to the reaction mixture, indicating a short lifetime of the mitosene semiquinone free radicals under aqueous conditions. In addition, enzymatic one-electron reduction of these mitosenes with either xanthine oxidase or purified NADPH cytochrome P450 reductase under anaerobic conditions showed no signals of the mitosene semiquinone free radicals. Subsequent cyclic voltammetry measurements demonstrated facilitation of the further one-electron reduction of the mitosene semiquinone free radicals in the presence of water in comparison with non-aqueous conditions. The present results strongly suggest that in the presence of water relatively stable hydroquinones are formed upon reduction of mitosenes. Consequently, the steady state concentrations of mitosene semiquinone free radicals will be lowered substantially in aqueous environment. Thus under physiological conditions, two-electron reduction and formation of the mitosene hydroquinone might be important in processes leading to DNA alkylation by these mitosenes.

AB - Chemical reduction of mitosenes under aerobic conditions in DMSO showed characteristic ESR signals of the mitosene derived semiquinone free radicals. However, these signals diminished strongly upon addition of water to the reaction mixture, indicating a short lifetime of the mitosene semiquinone free radicals under aqueous conditions. In addition, enzymatic one-electron reduction of these mitosenes with either xanthine oxidase or purified NADPH cytochrome P450 reductase under anaerobic conditions showed no signals of the mitosene semiquinone free radicals. Subsequent cyclic voltammetry measurements demonstrated facilitation of the further one-electron reduction of the mitosene semiquinone free radicals in the presence of water in comparison with non-aqueous conditions. The present results strongly suggest that in the presence of water relatively stable hydroquinones are formed upon reduction of mitosenes. Consequently, the steady state concentrations of mitosene semiquinone free radicals will be lowered substantially in aqueous environment. Thus under physiological conditions, two-electron reduction and formation of the mitosene hydroquinone might be important in processes leading to DNA alkylation by these mitosenes.

KW - Alkylation

KW - Animals

KW - Antineoplastic Agents

KW - Borohydrides

KW - DNA

KW - Dimethyl Sulfoxide

KW - Electron Spin Resonance Spectroscopy

KW - Free Radicals

KW - Mitomycins

KW - NADPH-Ferrihemoprotein Reductase

KW - Oxidation-Reduction

KW - Quinones

KW - Rats

KW - Solutions

KW - Water

KW - Xanthine Oxidase

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.3109/10715769509147533

DO - 10.3109/10715769509147533

M3 - Article

VL - 22

SP - 109

EP - 121

JO - Free Radical Research

JF - Free Radical Research

SN - 1071-5762

IS - 2

ER -